In the late 1990s, hotelier André Balazs put his fashionable stamp on New York’s tranquil Shelter Island by turning a vintage motel into a buzz-worthy inn. More than 10 years later, the property has managed to retain its chic sensibility without disrupting the island’s laid-back vibe.

The 80-year old island staple, where Charles Lindbergh once visited, gave its 107 rooms a multimillion dollar overhaul in 2009. The property has a scaled-down replica of the town’s famous lighthouse, not to mention three pools, four tennis courts, a spa, and a marina.

On the western corner of New York's Shelter Island, the Pridwin offers guests panoramic views of Southold Bay and easy access to Crescent Beach. Some of the rooms and cottages come with water views, while others have fireplaces.

The north fork of Long Island—a 30-mile strip of oceanside plains dotted with farms and boutique wineries—is the quiet alternative to the nearby Hamptons. Overlooking trellises of grapevines, the four-room Shinn Estate Farmhouse is a place of respite for urban epicures.